1. Field of the Invention
The instant invention relates to a novel class of acylaminoorganosilicon compounds and their use as coupling agents. More specifically, the novel class of acylaminoorganosilicon compounds are those containing a fatty ethenoid substituent.
2. Prior Art
Acylaminoorganosilicon compounds have been generally known since the pioneering work performed by Morehouse as reported in U.S. Pat. Nos. 2,929,829 and 2,928,858. The novel acylaminoorganosilicon compounds taught in these references were considered useful as, among other things, acid-base indicators; additives for silicon products, such as oils and gums; thermosetting resins for coating materials; and ultraviolet ray absorbers.
Subsequent to the work performed by Morehouse, improvements based on new and useful acylaminoorganosilicon compounds were discovered. In U.S. Pat. No. 3,249,461, the use of a conjugated olefin containing acylaminoorganosilicon compounds was taught as effective fiber glass reinforcing agents. In U.S. Pat. No. 3,681,266, a distinct class of acylaminoorganosilicon compounds was fluorine modified to provide a coating material that is useful as a water repellant. In U.S. Pat. No. 3,720,699, a new and useful class of haloorganoacylaminoorganosilicon compounds are reported to be useful as a coating material.
A variance on the theme, U.S. Pat. No. 3,755,354 is directed to amide acid and imido-substituted organosilicon compounds that are reportedly useful as glass fiber coupling agents. In a closely related U.S. Pat. No. 3,787,439, imido-substituted organopolysiloxanes were disclosed, including conjugated, unsaturated acylaminoorganosilicon compounds, as additives for glass fibers.
In U.S. Pat. No. 3,959,327, acrylaminoorganosilicon compounds with thio-containing substituents were reported as plasticizers and coupling agents.
A new class of complex acylaminoorganosilicon compounds was reported in U.S. Pat. Nos. 4,209,455 and 4,284,548. In each the mono- and bis-silanes were characterized by a single acylamino group and at least one secondary or tertiary aminoorgano group. These novel compositions were considered useful in fiber sizes.
In U.S. Pat. No. 3,746,738, acylaminoorganosilicon compounds that contained various pendant silanes were described as useful glass fiber sizes.
In U.S. Pat. No. 3,537,832, silylated polymers were prepared by amidation of acid chloride modified polymers with aminoorganosilanes for use as coating materials.
Finally, CA 84:59633W teaches a stearoyl and oleoyl acylaminoorganosilicon compounds.
Although the art is replete with improvements in and modifications of acylaminoorganosilicon compounds, it is believed that the instant fatty ethenoid acylaminoorganosilicon compounds containing bis-silane and/or multiple unsaturation in the fatty constituents are novel and that their use as coupling agents is also novel.